Lithium Chloride → Tert-butyl 4-(2-(3-methoxyphenyl)oxazol-4-yl)phenylcarbamate

HRID 643643Notes

Reaction equation

HRID 643643 reaction equation
FC(F)(F)S(O[C:7]1[N:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[O:10][CH:11]=1)(=O)=O.C[Sn](C)(C)[C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:26][CH:25]=1.[Li+].[Cl-]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:9]2[O:10][CH:11]=[C:7]([C:24]3[CH:25]=[CH:26][C:27]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[CH:28][CH:29]=3)[N:8]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 19692795Tert-butyl 4-(trimethylstannyl)phenylcarbamateHCID 592629762-(3-Methoxyphenyl)oxazol-4-yl trifluoromethanesulfonate

Product 1

HCID 59262979Tert-butyl 4-(2-(3-methoxyphenyl)oxazol-4-yl)phenylcarbamateYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a sealable tube, 17 (436 mg, 1 eq), tert-butyl 4-(trimethylstannyl)phenylcarbamate (600 mg, 1.25 eq), LiCl (280 mg, 4 eq), Pd(PPh3)4 (77 mg, 5%) were mixed in 10 ml of dioxane. The tube was sealed and heated for 1 night at 100° C., cooled to RT, evaporated and purified by flash chromatography (SiO2, hexane/AcOEt, 85/15) giving 18 as a white solid in 73% yield.

Workup

  1. customThe tube was sealed
  2. temperaturecooled to RT
  3. customevaporated
  4. custompurified by flash chromatography (SiO2, hexane/AcOEt, 85/15)

Sources & evidence

ORD record
ord-353e6c210d474b88819ca5b99aacaeca
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

Loading…